Owning a STR isn't just about the tax advantages but also comes with the responsibility of running (unless you decide to pay $ monthly to have a property manager, which comes its own challenges). 

I've even thought of buying a rental house to offer to a full time employee to move to this area but I'm not sure if that would just create more headaches in the long run) Employer responsibilities; payroll taxes, administration and audits.

On weekends, late morning - late afternoon (11am-4pm) seems to get the best response rate for me.

I had to school a so called wholesaler last week on his comps, lol!

I worked with a few partners and we didn't have our responsibilities laid out before we began, so the project took much longer than it should've and we incurred more holding costs than we needed to.

-Any other specific tips for the Tampa market would be welcomed!

You will get better responses if you dial in what it is you're looking for. 

And a little tip...if you can move all or even some of the properties you own into a trust, LLC, or whatever entity is right for you, the DTI clears up and you look favorable to lenders.

It's very rare a doctor gets his actual fee. 

So as a general rule: "yes," you'll want to purchase through an LLC, but "no," you (usually) won't have less liability if the proverbial hits the fan.Appreciate the response!